Generational Selling in Retail Technology with Tyler Wells

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Kate Orara:
Hey there, retail tech enthusiasts! Welcome to the Rising Stars podcast, your go-to source for all things retail technology and the ever-evolving world of point of sale. I’m your host, Kate Orara, Partner Development Manager at Star Micronics, and I am thrilled to be your guide on this exciting journey. Here at Rising Stars, we’re not just keeping up with the trends—we’re setting them. We dive deep into the tech landscape with global industry leaders, unpacking strategies and discussing the latest innovations that shape the future of retail IT.

Whether you’re a tech aficionado, business owner, or just curious about the dynamic world of retail, this podcast is your backstage pass to insider knowledge. And hey, it’s not just about the tech—it’s about the community. Join me and the Star Micronics team as we lead and innovate, shaping a brighter future for the retail, hospitality, and cannabis industries, as well as beyond. Together, we rise. So hit that subscribe button, stay in the loop, and let’s make waves in the retail tech space. This is the Rising Stars podcast, where innovation meets inspiration. Let’s rise together!

Kate Orara:
Well, hello, everybody, and welcome back to another episode of the Rising Stars podcast. I’m your host, Kate Orara, and I’m so happy you’re here today. I’m really excited because I’ve got a really good friend of mine from the industry, Tyler Wells, who is the ISV and Strategic Partner Manager at MicroTouch. Tyler, welcome!

Tyler Wells:
Thanks, Kate! Like you said, we’ve known each other for quite a few years now—almost going on a decade. Back when I was working at Mimo Monitors as their Business Development Manager, I was in the tech hardware space for quite a while. At MicroTouch, I manage our ISVs and strategic partners. As we go to market with solutions, end users and resellers are always asking for a complete solution, not just a touchscreen. So I manage the partners to build a solution through our reseller group, making sure we have great customer service and grow everyone’s business.

ISVs for hardware companies are an integral part of business growth and understanding the market. They’re an influential piece of our business, and I’m proud to work with them through a company like MicroTouch. Traditionally, we’ve worked with ISVs in North America and Latin America, but we’re also moving into self-service and QSR POS in Europe and Africa. It’s been exciting. I’ve been with the MicroTouch team since their inception three years ago, and it’s been a fun ride watching our prominence grow in the market.

Kate Orara:
It’s been fun watching not only their development but also your development, Tyler. You’ve been on the 40 Under 40, now 50 Under 50, and you’re still not even 40 yet! Your girl here has been in the 40s for a little while now. Just to let you know—the water’s fine when you get here. [laughs]

Tyler Wells:
[laughs] Well, I appreciate that, Kate. It’s really thanks to the mentors and partners I’ve had throughout my career. They’ve set me up to succeed, and with resources like the RSPA and our partners, we’re surrounded by great people who support and help our growth. That’s for sure.

Kate Orara:
Absolutely! So, the structure of this podcast is usually interview-based, but today, we’re doing things a little differently. Tyler and I were fortunate to be on a panel together at RSPA’s RetailNOW, a couple of weeks ago, which was in Vegas. If you’re listening to this in the future, that’s the context. We were on a panel titled “Generational Selling,” where we shared takeaways for resellers and software partners on how to sell to different generations.

If you weren’t at the panel, let me tell you—it was one of the most passionate and active sessions I’ve ever been a part of in my nearly 19 years in this channel. What about you, Tyler?

Tyler Wells:
Yes, it was incredibly passionate. And what stood out to me was that it wasn’t even the panelists who spoke the most—it was the audience! We were excited about the topic, and so was the crowd. They started asking questions, and before we knew it, the whole room was engaged. It was great to see that this is a hot topic for the channel.

Kate Orara:
Exactly! What surprised me was how many different generations are in the workforce right now. Tyler and I are both Millennials, but even within that, we have different experiences because Millennials span a broad range from 1981 to 1996. Tyler, do you want to touch on some of the key generational characteristics?

Tyler Wells:
Sure. Baby Boomers, born from 1946 to 1964, really value loyalty and face-to-face communication. They prefer to make deals with a handshake or verbal agreement. Generation X, born from 1965 to 1980, is independent, pragmatic, and values work-life balance. They were the first to adopt technology like cell phones and the internet.

Millennials, from 1981 to 1996, have never really known a world without technology. We grew up with cell phones and adapted to the digital age. And Gen Z, born from 1997 onwards, were practically born with a cell phone in hand! They’re digital natives, but that doesn’t always mean they’re the best communicators in person.

Kate Orara:
Exactly! My kids don’t even know what a landline is. I remember explaining a dial tone to them at a soccer tournament—it was hilarious. And I think that really ties into how each generation prefers to communicate. Boomers and Gen X are more likely to pick up the phone, while Millennials and Gen Z might prefer texting or emails. So, how do you adjust your communication strategy for each generation?

Tyler Wells:
For Boomers and Gen X, I keep things clear, concise, and direct. They prefer straightforward communication—no room for misinterpretation. For Millennials and Gen Z, I’m more relaxed and conversational, but you still have to be mindful of tone, especially with texts and emails. Emojis can help, but they can also be misinterpreted.

Kate Orara:
Right! And when it comes to building trust, each generation values it differently. What are some strategies for building trust with these different groups?

Tyler Wells:
Authenticity is key. Cold calling doesn’t work as well as it used to, because people are wary of scams and phishing. You have to build trust through consistent communication—whether it’s email, phone, or in person—and show that you’re genuinely invested in solving their problems.

Kate Orara:
Absolutely. And let’s talk about confrontation—Millennials and Gen Z tend to avoid it. How can we encourage these generations to deal with issues head-on?

Tyler Wells:
Setting the right expectations is crucial. If there’s an issue, don’t shy away from it. Address the problem directly and explain how you plan to fix it. This turns an awkward conversation into an opportunity to build even more trust.

Kate Orara:
Exactly. It’s all about owning the problem and showing that you care about the outcome. Now, let’s shift gears to sales techniques. What aspects of a product or service should be emphasized to appeal to each generation’s priorities?

Tyler Wells:
Loyalty is a big factor across all generations, but it looks different depending on the age group. Boomers and Gen X are loyal to brands they trust, while Millennials and Gen Z are more likely to shop around using the internet and apps to compare options. Keeping them loyal requires innovation and competitive pricing.

Kate Orara:
Yes! My husband loves to compare car insurance quotes, even though I’m more loyal to brands that have treated us well. It’s funny how Millennials and Gen Z rely on technology for these decisions.

Tyler Wells:
Exactly. And speaking of technology, overcoming stereotypes is important. You can’t assume that Gen X won’t understand new tech, or that Gen Z won’t appreciate a personal touch. Each client is unique, so we need to approach them as individuals.

Kate Orara:
Totally agree. Now, let’s talk about future trends in retail tech. What do you see coming that could help bridge generational gaps?

Tyler Wells:
AI, VR, and AR are the big ones right now. AI, for example, is transforming how we interact with customers and streamline processes. But we need to make sure we’re educating older generations on how to use these technologies safely. We need to address cybersecurity concerns while also showing how these tools can make life easier.

Kate Orara:
Absolutely. AI is here to stay, and while there’s some hesitancy—especially among Boomers and Gen X—it’s all about showing the benefits without overwhelming them.

Tyler Wells:
Exactly. We need to provide the right education and support for everyone to feel comfortable adopting these new technologies.

Kate Orara:
Well, Tyler, I think we’ve covered a lot today. Anything else you’d like to add before we wrap up?

Tyler Wells:
No, I think we did a great job covering the key points. It’s been a great conversation, and I’m always happy to talk about these topics.

Kate Orara:
Thanks so much, Tyler! And thank you to our listeners for tuning in. Be sure to subscribe to our podcast on your favorite platform—whether it’s Spotify, Apple Podcasts, or anywhere else—and leave us a review. Let us know what you’d like to hear more about. I’d love to have Tyler back for a part two! Thanks again, everyone, and until next time, this is Kate Orara signing off. Together, we rise!

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